Addressing executive swoop-ins

This was first published on my mailing list The Looking Glass. Every week, I answer a reader’s question.

Photo by James West

Q: How can I address direction from upper management that I suspect will harm or even derail the product? i.e. What is the most effective way to push back on an executive order that I or the team feel is detrimental to the product?

This is a situation that’s unfortunately rather common. A project is in development. You and the team believe in what you’re doing, and things are coming together nicely. Then, late in the game, out of the blue, a company leader, perhaps even the CEO, swoops in with a product idea that you don’t agree with, but now you feel responsible to act on it.

I’ve experienced this myself a few times, both as a recipient, and also quite frankly as the swooper. It’s no mystery why this happens — everyone wants the product to be successful, and everyone has different opinions about the best path forward. Typically this cognitive diversity makes teams stronger, as it’s great to have different perspectives, data, and intuitions as input. However, it can feel pretty randomizing and perhaps even demoralizing when a leader higher up in your management chain comes in after work is already well underway and gives direction that runs counter to the team’s plans.

How can you address this swoop-in, arrive at a good solution, and bridge the gap between your team and your execs?

First, a few Don’ts.

Don’t tell your team “The boss wants us to do this, so I guess we have to do it”

This is bad management for so many reasons. You’re not taking ownership of the plans, but instead you’re leaking your power. You’re not building strong relationships, but instead you’re throwing the company’s leadership under the bus and pointing fingers of blame. You’re eroding trust in both directions.

Don’t ignore it

On the complete opposite end of the spectrum, it’s also a mistake to ignore feedback from a company exec, with a sense that “I know better”.

If you hope the suggestion was just an off-hand comment that will go away, there’s a chance you’re right. But nobody appreciates the “pocket veto.” You’re putting your team at risk of going even deeper down your current path and needing to make a more painful change later.

Don’t blindly follow direction that you don’t fully understand

Following direction that you don’t fully agree with is sometimes warranted. However, following an order that you don’t understand is akin to following the letter of the law instead of the spirit of the law, and could leave you missing the point.

At a minimum, it is worth asking clarifying questions about any direction that you disagree with, so that you know what they mean in addition to what they say.

As an example, if an executive says “this button should be higher on the page”, don’t just say “yes” and make the change. Dig a layer deeper to ensure you know what they want to achieve. Sometimes this is as simple as asking “Why do you think so?” or interpreting the direction at a higher level and rephrasing it as a question: “Are you concerned people won’t see the call to action where it’s currently located?”

Don’t frame the situation as “us” vs. “them”

Approaching any situation where there’s disagreement, things will escalate quickly and all parties may turn defensive if you don’t fully embrace that you’re all on the same team.

Product direction isn’t about winning or losing, or your ideas vs. the exec’s ideas. You all what the same thing — a successful product. And you each bring a different set of strengths to the table. You bring domain specific knowledge. Your executive may bring a broader perspective of what the product is meant to achieve.

So, how can you work together?

Find Common Ground

Your team is hard at work. You’ve spent a lot of time researching opportunities, iterating on ideas, and you’re confident in your plans. Now an executive, who likely hasn’t spent as much time thinking about or working on these problems, feels they have a better idea you should consider instead.

Perhaps their suggestion goes against what your research or data indicates is the right direction. Or perhaps it’s a fine idea, but could be more effort than it is worth, and doesn’t seem important enough to prioritize doing right now.

Whatever the reason for why you disagree, you’ll never make progress in a discussion if all your responses start with “No.”

Figure out where you have common ground. Do you agree what problem you’re trying to solve? Do you agree on how you know this is the right problem, and the data/research informing your strategy? Do you agree on how you will measure success? Before getting bogged down in specific implementation details, ensure that you’re aligned on the larger questions motivating each of your perspectives.

Often this exercise will lead you to realize the disconnect isn’t about where the button should be, but something else entirely. Perhaps you’re optimizing for different things. Perhaps one of you is missing a critical piece of info about how this work fits into the broader product experience. If you approach this conversation with a mind towards connecting, rather than as an argument trying to prove your point, you’ll almost certainly end up understanding the feedback better and feeling closer. With any luck, you’ll realize there’s a compromise that works for everyone.

If not, the next best thing is to “disagree and commit.” You may not yet be convinced, but the show must go. The faster you try something, even if you don’t think it’s the best course, the faster you’ll learn.

Prevent swooping entirely by sharing early and often

A habit of an effective leader is to ensure your plans are known, understood, and aligned with all the key stakeholders. Any time swooping is happening, this is often a symptom that you went too far down a path without getting all the required input and buy-in.

Seek input on roadmaps and designs, sharing your early thinking and ideas. Take ownership of scheduling reviews proactively. Give your executives an opportunity to contribute to at every stage, and aim to get confirmation from anyone who could potentially swoop-in later that “Yes, I understand and agree with these plans.” Be extra vigilant if you sense hesitation about your plans, and follow up 1:1 to understand where the disconnect may be.

Although this is certainly easier said than done, it’s the ounce of prevention that’s worth a pound of cure, and will likely unearth feedback at a time when changes aren’t as costly as a late-stage swoop.


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